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Search results; Over 1,000 homes in Winter Park

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Guest favourite
Apartment in Winter Park
Modern Winter Park Condo w/ Community Hot Tub!
2 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
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4.85 out of 5 average rating, 54 reviews
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Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds
18–23 Oct
4.97 out of 5 average rating, 37 reviews
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Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds
6–11 Oct
New place to stay
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Featured hotel
Hotel in Winter Park
Gravity Haus Winter Park, Superior king twin trun.
1 bedroom
1–6 Oct
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Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds
4–9 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds
13–18 Oct
4.92 out of 5 average rating, 79 reviews
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Guest favourite
Apartment in Winter Park
Winter Park Ski Resort - Top Floor
1 bedroom, 1 sofa bed
1–6 Oct
4.98 out of 5 average rating, 42 reviews
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Guest favourite
Apartment in Winter Park
One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit
1 bedroom, 2 beds
4–9 Oct
4.88 out of 5 average rating, 221 reviews
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Top guest favourite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 queen bed
1–6 Oct
4.98 out of 5 average rating, 499 reviews
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Top guest favourite
Apartment in Winter Park
Cozy Winter Park Riverfront Studio~ Walk Downtown
2 beds
4–9 Oct
5.0 out of 5 average rating, 121 reviews
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Superhost
Home in Winter Park
WP Resort Villa 509 - Hot Tub - Views - Theatre
4 bedrooms, 6 beds
1–6 Oct
New place to stay
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Top guest favourite
Apartment in Winter Park
Winter Park Condo on the River: Walk to Downtown!
1 bedroom, 2 beds
4–9 Oct
4.99 out of 5 average rating, 125 reviews
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Guest favourite
Home in Winter Park
Winter Park Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds
11–16 Oct
4.78 out of 5 average rating, 23 reviews
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Top guest favourite
Apartment in Winter Park
Best Views In WinterPark | FamilyFriendly | Garage
3 bedrooms, 6 beds
5–10 Oct
5.0 out of 5 average rating, 131 reviews
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Guest favourite
Apartment in Winter Park
Stylish Studio on Main Street in Winter Park
1 king bed
6–11 Oct
4.9 out of 5 average rating, 98 reviews
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Guest favourite
Flat in Winter Park
NEW Ski-In Ski-Out Romantic Studio for Two
2 king beds
1–6 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Apartment in Winter Park
Ski In/Ski Out - Modern Cozy Condo in Winter Park
2 beds
13–18 Oct
4.9 out of 5 average rating, 251 reviews
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Guest favourite
Flat in Winter Park
Ski in / Ski out at Winter Park - pool & hot tub
2 beds
1–6 Oct
4.9 out of 5 average rating, 20 reviews
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Guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds
10–15 Oct
4.97 out of 5 average rating, 36 reviews